{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T18:53:47Z","timestamp":1785437627020,"version":"3.56.0"},"reference-count":45,"publisher":"International Union of Crystallography (IUCr)","issue":"8","license":[{"start":{"date-parts":[[2023,7,21]],"date-time":"2023-07-21T00:00:00Z","timestamp":1689897600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2023,7,21]],"date-time":"2023-07-21T00:00:00Z","timestamp":1689897600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr E Cryst Commun","Acta Cryst E","Acta Cryst Sect E","Acta Crystallogr E","Acta Crystallogr Sect E","Acta Cryst E Cryst Commun","Acta Cryst Sect E Cryst Commun"],"accepted":{"date-parts":[[2023,7,10]]},"published-print":{"date-parts":[[2023,8,1]]},"abstract":"<jats:p>\n                    In the title compounds, C\n                    <jats:sub>22<\/jats:sub>\n                    H\n                    <jats:sub>16<\/jats:sub>\n                    FNO\n                    <jats:sub>2<\/jats:sub>\n                    S\n                    <jats:sub>2<\/jats:sub>\n                    (\n                    <jats:bold>I<\/jats:bold>\n                    ) and C\n                    <jats:sub>26<\/jats:sub>\n                    H\n                    <jats:sub>20<\/jats:sub>\n                    FNO\n                    <jats:sub>2<\/jats:sub>\n                    S\n                    <jats:sub>2<\/jats:sub>\n                    (\n                    <jats:bold>II<\/jats:bold>\n                    ), the benzothiophene rings are essentially planar with maximum deviations of 0.009\u2005(1) and 0.001\u2005(1)\u2005\u00c5 for the carbon and sulfur atom in compounds\n                    <jats:bold>I<\/jats:bold>\n                    and\n                    <jats:bold>II<\/jats:bold>\n                    , respectively. In\n                    <jats:bold>I<\/jats:bold>\n                    , the thiophene ring system is almost orthogonal to the phenyl ring attached to the sulfonyl group, with a dihedral angle of 77.7\u2005(1)\u00b0. In compound\n                    <jats:bold>I<\/jats:bold>\n                    , the molecular structure is stabilized by weak C\u2014H...O intramolecular interactions formed by the sulfone oxygen atoms, which generate two\n                    <jats:italic>S<\/jats:italic>\n                    (5) ring motifs. In the crystal of\n                    <jats:bold>I<\/jats:bold>\n                    , N\u2014H...O hydrogen bonds link the molecules into\n                    <jats:italic>R<\/jats:italic>\n                    <jats:sup>2<\/jats:sup>\n                    <jats:sub>2<\/jats:sub>\n                    (8) rings, which are connected into a\n                    <jats:italic>C<\/jats:italic>\n                    (10) chain\n                    <jats:italic>via<\/jats:italic>\n                    C\u2014H...F hydrogen bonds. Intermolecular C\u2014H...\u03c0 interactions are also observed. In compound\n                    <jats:bold>II<\/jats:bold>\n                    , the molecules are linked\n                    <jats:italic>via<\/jats:italic>\n                    C\u2014H...O and C\u2014H...F hydrogen bonding, generating infinite\n                    <jats:italic>C<\/jats:italic>\n                    (11) and\n                    <jats:italic>C<\/jats:italic>\n                    (13) chains running parallel to [010].\n                  <\/jats:p>","DOI":"10.1107\/s2056989023006096","type":"journal-article","created":{"date-parts":[[2023,7,17]],"date-time":"2023-07-17T04:58:26Z","timestamp":1689569906000},"page":"741-746","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":4,"title":["Crystal-structure determination and Hirshfeld surface analysis of two new thiophene derivatives: (\n                    <i>E<\/i>\n                    )-\n                    <i>N<\/i>\n                    -{2-[2-(benzo[\n                    <i>b<\/i>\n                    ]thiophen-2-yl)ethenyl]-5-fluorophenyl}benzenesulfonamide and (\n                    <i>E<\/i>\n                    )-\n                    <i>N<\/i>\n                    -{2-[2-(benzo[\n                    <i>b<\/i>\n                    ]thiophen-2-yl)ethenyl]-5-fluorophenyl}-\n                    <i>N<\/i>\n                    -(but-2-yn-1-yl)benzenesulfonamide"],"prefix":"10.1107","volume":"79","author":[{"given":"S.","family":"Madhan","sequence":"first","affiliation":[{"id":[{"id":"https:\/\/ror.org\/04jmt9361","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"M.","family":"NizamMohideen","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/04jmt9361","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vinayagam","family":"Pavunkumar","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/04jmt9361","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Arasambattu K.","family":"MohanaKrishnan","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/04jmt9361","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2023,7,21]]},"reference":[{"key":"zn2029_bb1","doi-asserted-by":"crossref","first-page":"680","DOI":"10.1002\/jhet.141","volume":"46","author":"Abdelhamid","year":"2009","journal-title":"J. Heterocycl. Chem."},{"key":"zn2029_bb2","first-page":"372","volume":"58","author":"Abdel-Rahman","year":"2003","journal-title":"Pharmazie"},{"key":"zn2029_bb3","doi-asserted-by":"crossref","first-page":"S1","DOI":"10.1039\/p298700000s1","volume":"2","author":"Allen","year":"1987","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"zn2029_bb4","first-page":"17","volume":"39","author":"Ansary","year":"2001","journal-title":"Bull. Faculty Pharm."},{"key":"zn2029_bb5","unstructured":"Bassindale, A. (1984). The Third Dimension in Organic Chemistry, ch. 1, p. 11. New York: John Wiley and Sons."},{"key":"zn2029_bb6","doi-asserted-by":"crossref","first-page":"2242","DOI":"10.1021\/jo9517555","volume":"61","author":"Bedworth","year":"1996","journal-title":"J. Org. Chem."},{"key":"zn2029_bb7","doi-asserted-by":"crossref","first-page":"1555","DOI":"10.1002\/anie.199515551","volume":"34","author":"Bernstein","year":"1995","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"zn2029_bb8","doi-asserted-by":"crossref","first-page":"6580","DOI":"10.1016\/j.tet.2005.04.048","volume":"61","author":"Bonini","year":"2005","journal-title":"Tetrahedron"},{"key":"zn2029_bb9","doi-asserted-by":"crossref","first-page":"757","DOI":"10.1016\/j.ejmech.2005.02.010","volume":"40","author":"Brault","year":"2005","journal-title":"Eur. J. Med. Chem."},{"key":"zn2029_bb10","unstructured":"Bruker (2016). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA."},{"key":"zn2029_bb11","doi-asserted-by":"crossref","unstructured":"Chen, H. J., Wang, W., l. Wang, G. F., Shi, L. P., Gu, M., Ren, Y. D. & Hou, L. F. (2008). Med. Chem. 3, 1316-1321.","DOI":"10.1002\/cmdc.200800136"},{"key":"zn2029_bb12","doi-asserted-by":"crossref","first-page":"849","DOI":"10.1107\/S0021889812029111","volume":"45","author":"Farrugia","year":"2012","journal-title":"J. Appl. Cryst."},{"key":"zn2029_bb13","doi-asserted-by":"crossref","first-page":"1384","DOI":"10.1016\/j.bmcl.2005.11.035","volume":"16","author":"Ferreira","year":"2006","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"zn2029_bb14","first-page":"298","volume":"33","author":"Gadad","year":"1994","journal-title":"Ind. J. Chem. Soc."},{"key":"zn2029_bb15","doi-asserted-by":"crossref","first-page":"1079","DOI":"10.1039\/b716510b","author":"Gather","year":"2008","journal-title":"Chem. Commun."},{"key":"zn2029_bb16","first-page":"99","volume":"99","author":"Gewald","year":"1966","journal-title":"Chem. Ber."},{"key":"zn2029_bb17","doi-asserted-by":"crossref","first-page":"655","DOI":"10.1016\/0192-0561(85)90149-3","volume":"7","author":"Gillespie","year":"1985","journal-title":"Int. J. Immunopharmacol."},{"key":"zn2029_bb18","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1107\/S2052520616003954","volume":"72","author":"Groom","year":"2016","journal-title":"Acta Cryst. B"},{"key":"zn2029_bb19","doi-asserted-by":"crossref","first-page":"542","DOI":"10.1016\/j.bmc.2007.08.066","volume":"16","author":"Grunewald","year":"2008","journal-title":"Bioorg. Med. Chem."},{"key":"zn2029_bb20","doi-asserted-by":"crossref","first-page":"11930","DOI":"10.1021\/ja903895s","volume":"131","author":"He","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"zn2029_bb21","doi-asserted-by":"crossref","first-page":"2346","DOI":"10.1021\/jm049541f","volume":"48","author":"Jarak","year":"2005","journal-title":"J. Med. Chem."},{"key":"zn2029_bb22","unstructured":"Jayatilaka, D., Grimwood, D. J., Lee, A., Lemay, A., Russel, A. J., Taylor, C., Wolff, S. K., Cassam-Chenai, P. & Whitton, A. (2005). TONTO - A System for Computational Chemistry. Available at: http:\/\/hirshfeldsurface.net\/"},{"key":"zn2029_bb23","doi-asserted-by":"crossref","first-page":"1081","DOI":"10.1021\/jm020450x","volume":"46","author":"Jordan","year":"2003","journal-title":"J. Med. Chem."},{"key":"zn2029_bb24","doi-asserted-by":"crossref","first-page":"1830","DOI":"10.1021\/cm702631r","volume":"20","author":"Justin Thomas","year":"2008","journal-title":"Chem. Mater."},{"key":"zn2029_bb25","first-page":"509","volume":"35","author":"Laddi","year":"1998","journal-title":"Indian Drugs"},{"key":"zn2029_bb26","doi-asserted-by":"crossref","first-page":"226","DOI":"10.1107\/S1600576719014092","volume":"53","author":"Macrae","year":"2020","journal-title":"J. Appl. Cryst."},{"key":"zn2029_bb27","doi-asserted-by":"crossref","first-page":"1198","DOI":"10.1107\/S2056989022010684","volume":"78","author":"Madhan","year":"2022","journal-title":"Acta Cryst. E"},{"key":"zn2029_bb28","doi-asserted-by":"crossref","first-page":"521","DOI":"10.1107\/S2056989023003821","volume":"79","author":"Madhan","year":"2023","journal-title":"Acta Cryst. E"},{"key":"zn2029_bb29","doi-asserted-by":"crossref","first-page":"2060","DOI":"10.1002\/adma.200305356","volume":"15","author":"Mazzeo","year":"2003","journal-title":"Adv. Mater."},{"key":"zn2029_bb30","doi-asserted-by":"crossref","first-page":"3814","DOI":"10.1039\/b704980c","author":"McKinnon","year":"2007","journal-title":"Chem. Commun."},{"key":"zn2029_bb31","first-page":"332","volume":"3","author":"Mishra","year":"2012","journal-title":"Der Pharmacia Sinica"},{"key":"zn2029_bb32","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1002\/jhet.5570170116","volume":"17","author":"Monge Vega","year":"1980","journal-title":"Heterocycl. Chem."},{"key":"zn2029_bb33","doi-asserted-by":"crossref","first-page":"4420","DOI":"10.1016\/j.bmcl.2008.06.040","volume":"18","author":"Nathan Tumey","year":"2008","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"zn2029_bb34","doi-asserted-by":"crossref","first-page":"62","DOI":"10.1016\/j.dyepig.2011.02.012","volume":"91","author":"Raposo","year":"2011","journal-title":"Dyes Pigments"},{"key":"zn2029_bb35","doi-asserted-by":"crossref","unstructured":"Russell, R. K. & Press, J. B. (1996). Comprehensive Heterocyclic Chemistry II, Vol. 2, edited by A. R. Katritzky, C. W. Rees & E. F. V. Scriven. pp. 679-729. Oxford: Pergamon Press.","DOI":"10.1016\/B978-008096518-5.00051-4"},{"key":"zn2029_bb36","first-page":"1","volume":"16","author":"Sabins","year":"1944","journal-title":"Sulfur Rep."},{"key":"zn2029_bb37","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Cryst. A"},{"key":"zn2029_bb38","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"zn2029_bb39","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1039\/B818330A","volume":"11","author":"Spackman","year":"2009","journal-title":"CrystEngComm"},{"key":"zn2029_bb40","first-page":"377","volume":"10","author":"Spackman","year":"2008","journal-title":"CrystEngComm"},{"key":"zn2029_bb41","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1107\/S2056989019016244","volume":"76","author":"Spek","year":"2020","journal-title":"Acta Cryst. E"},{"key":"zn2029_bb42","doi-asserted-by":"crossref","first-page":"308","DOI":"10.1107\/S2056989019001129","volume":"75","author":"Tan","year":"2019","journal-title":"Acta Cryst. E"},{"key":"zn2029_bb43","unstructured":"Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17. University of Western Australia. http:\/\/hirshfeldsurface.net"},{"key":"zn2029_bb44","doi-asserted-by":"crossref","first-page":"920","DOI":"10.1107\/S0021889810022120","volume":"43","author":"Westrip","year":"2010","journal-title":"J. Appl. Cryst."},{"key":"zn2029_bb45","doi-asserted-by":"crossref","first-page":"7246","DOI":"10.1021\/ja071760d","volume":"129","author":"Zhan","year":"2007","journal-title":"J. Am. Chem. Soc."}],"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2023\/08\/00\/zn2029\/zn2029.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2023\/08\/00\/zn2029\/zn2029.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,13]],"date-time":"2025-01-13T06:26:06Z","timestamp":1736749566000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2056989023006096"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,7,21]]},"references-count":45,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2023,8]]}},"alternative-id":["S2056989023006096"],"URL":"https:\/\/doi.org\/10.1107\/s2056989023006096","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2056989023006096\/zn2029sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989023006096\/zn2029Isup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989023006096\/zn2029IIsup3.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989023006096\/zn2029Isup4.cml","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989023006096\/zn2029IIsup5.cml","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"value":"2056-9890","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,7,21]]},"assertion":[{"value":"Acta Crystallographica Section E: Crystallographic Communications","order":0,"name":"journal","label":"Publication","explanation":{"URL":"https:\/\/journals.iucr.org\/e"},"group":{"name":"general","label":"General"}},{"value":"research communications","order":1,"name":"content_type","label":"Content type","explanation":{"URL":"https:\/\/journals.iucr.org\/e\/services\/notesforauthors.html"},"group":{"name":"general","label":"General"}},{"value":"Available","URL":"https:\/\/scripts.iucr.org\/cgi-bin\/citedin?zn2029","order":2,"name":"article_metrics","label":"Article metrics","group":{"name":"general","label":"General"}},{"value":"Yes","order":0,"name":"peer_reviewed","label":"Peer reviewed","group":{"name":"peer_review","label":"Peer review"}},{"value":"Single blind","order":1,"name":"review_process","label":"Review process","group":{"name":"peer_review","label":"Peer review"}},{"value":"8 May 2023","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"10 July 2023","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"21 July 2023","order":2,"name":"published_online","label":"Published online","group":{"name":"publication_history","label":"Publication history"}},{"value":"This article has supporting information","name":"supplementary_materials","label":"Supplementary materials","explanation":{"URL":"https:\/\/scripts.iucr.org\/cgi-bin\/sendsup?zn2029"}},{"value":"\u00a9 2023 Madhan\n                      et al.","order":0,"name":"copyright","label":"Copyright","explanation":{"URL":"https:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},"group":{"name":"copyright_and_licencing","label":"Copyright and licencing"}},{"value":"Creative Commons Attribution (CC-BY)","order":1,"name":"license","label":"Licence","explanation":{"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},"group":{"name":"copyright_and_licencing","label":"Copyright and licencing"}}]}}